Opsy Guide to Ops Leadership

Operations leaders are a crucial part of any successful business, but they come in a whole host of shapes and sizes.

There are Directors, VPs, COOs, and another half-dozen titles that all seem to translate to “most senior ops person at the company,” yet have different responsibilities.

The scope of an ops leader’s role can vary a lot depending on their background, the nature of the business, company size, and even the strengths and skills of the company’s CEO.

So what does that mean for an operations pro who wants to understand how they can grow into one of these roles? Or a founder who doesn’t quite know what role makes sense for them to hire?

✨ Entering the Opsy Guide to Operations Leadership! ✨

I’ve talked to dozens of ops leaders about their roles and responsibilities, their skills, and what they wish they had known before they took on their current role. And we’re going to break it all down together!

At a high level, an operations leader is someone who understands the business priorities and helps the team reach their goals.

There are a lot of different titles that this person can have but there tend to be two big differentiators:

• Team size — Are they managing one team or multiple teams? And are those team members entry-mid level professionals? Or are they senior specialists leading their own function?
• Company size — How big is the company? And, if VC-backed, what stage are are they at?

These two factors help define the scope of the leader's responsibility. Which, in turn determines their title and pay.

Let's start at the top, shall we?

Chief Operating Officer (COO)

The Chief Operating Officer, or COO, is a top-level leader. When the company and its scope of work get too big for one leader to manage, a COO can oversee multiple leaders who are responsible for their own business area.

For this reason, you won't find many COOs at smaller companies—at least, not without a co-founder title. COOs are most valuable at mid-large sized organizations that have multiple layers of management because their ultimate goal is to be a strategic advisor to the CEO, lead multiple business areas, and focus on strategy at the highest level.

COOs rarely execute projects themselves, but they ensure that work gets done by providing crucial business insight, unblocking their teams, and reallocating resources. They're more focused on strategy and people management than being "in the weeds" and completing specific tasks.

Their exact areas of responsibility (and the teams they oversee) can vary greatly based on the exact company and its needs, as well as the needs and strengths of its CEO. It's most common to see them oversee "back office" functions like HR/People Ops, Finance, Legal, and Customer Support but, depending on the individual leader's background, it's also not unheard for them to lead Marketing, Product, or even Engineering.

In their words —

Dianna Moore, Runner: "Operations is truly taking the mission and values of a company and operationalizing it—not just the bottom line and how you make money, but also the kind of culture you want to create, how people feel about working with you... I see a large part of my role as removing roadblocks for the team [so we can] align our decisions and our actions with that business objectives."

Kristy Bayley, Yieldly: A COO is a conductor of the orchestra—leading from the front to ensure that each team knows the direction, the role, the plan, the process, and the timing. We enable the team to do what they do best. [We're also] often seconded into a team to help get them through a project, or take on a component of work that is currently not ideal, uplift it, and then return it back to the team.

Barrett Brooks, Good Coffee: "I think the number one thing I love [about the COO role] is the breadth. At ConvertKit, everything but Product reported in to me so I got to lead engineering, marketing, customer success, ops, and data. On any given day, I might be talking about everything from building out a feature that we're supposed to deliver, to conversion optimization and ad campaigns, to how to get more efficient in our outsourced customer service function, to, like, our data infrastructure. All of that could just be literally one day... Really, my main role is to ask good questions, provide global business insight to a given conversation, and then allow people to go do their jobs."

Vice President of Operations

A Vice President (or VP of Operations) is a senior leader and a key member of a company's executive team.

They are most often found at:

• Mid-stage startups who have product-market fit and are focused on scaling and
• Later stage companies that have grown so big that they need multiple, specialized VPs reporting into the COO.

A Vice President should oversee multiple teams or business functions just like a COO but they still have one foot in the execution world. They often take on one-off "special projects" that have a set timeframe and/or don't have a clear owner. For example, rolling out a new department, taking over leadership of a team that just lost its leader, managing a one-off project, and so on.

A VP of Ops doesn't have the same governance responsibilities of a COO, but is still a crucial member of the leadership team and a driver of the company strategy. This is the biggest difference between a VP and a Director—the latter contributes to company strategy but likely doesn't drive it to the same degree.

In their words —

Clare Austin, Avicado: "My role is to serve my team and help them be as effective and efficient as possible. I try to provide guidance on initiatives we are working on and remove blockers to ensure they can meet our overarching goal of making it easier for both the internal team to work and for clients to work with us.

My experience working with VPs in a larger org has been that the VPs interact mainly with other VPs and focus on long range planning. I prefer [the structure we have at Avicado] that enables me to participate in the day-to-day and provide insight into strategy and work on long range plans."

Megan Bianco, Scott's Cheap Flights: "Goal setting is a big part of what I do. OKRs, strategy, internal comms, tax compliance, legal, and finance—they are my world. And then I have a team of people way smarter than me that lead member success, data, people ops, and talent acquisition. And at the end of the day, when there isn't a super clear owner, I take on that work."

Director/Head of Operations

Operations leaders at smaller companies, especially early stage startups, are usually titled Director of Operations or Head of Operations.

A Head of Ops is likely to manage a small team but still do a lot of operations work themselves. Whereas a Director of Ops usually has more distance from executing their own tasks and a larger plate of management duties.

The difference between the two is minimal though, and really comes down to team size and the ratio of people management and execution. At least in theory! In practice, many companies use these titles interchangeably and it can really come down to preference and established naming conventions within the org.

In their words —

Cathy Dinas, Director of Operations at Backstage Capital:

Deanna Sinclair, Head of Operations at Polly: "I am responsible for the oversight, management and execution of areas/projects associated with the day-to-day functions of the business. This includes finance, legal, security, business and people operations.  I am also a member of the Leadership Team where I also contribute to strategic product and business decisions."

Chief of Staff

The newest kid on the block! The Chief of Staff exists a little bit outside of the hierarchy for these other roles, but is definitely an operations leader. It's also the role that I see founders, in particular, get really confused by.

Which makes sense! Often, founders know they need help with ops but they don't know exactly what kind of help they need and different advisors recommend different solutions—a Head of Ops, an EA, a Chief of Staff, etc.

The truth is that, functionally, a Chief of Staff exists somewhere in the space between a Head/Director of Operations and an Executive Assistant. They are an extension of their "principal" (usually a Founder, but sometimes another executive) and they often work with an assistant to free up that person to really excel in the mission critical stuff. The assistant takes on the admin like inbox management and scheduling, and the CoS usually takes on more strategic projects. But, unlike a Head of X, they work cross-functionality across a bunch of different areas.

This means that Chiefs of Staff have exposure to every department and a birds-eye view of the business. Lots of operators use it as a "tour of duty" to learn from a smart founder, before moving on to another role or even becoming a founder themselves. Few people stay a CoS for their whole career... but it's still a new-ish role so that may change!

In their words — 

Emilie Eros, Trustpage: "Chiefs of Staff roles vary quite a bit depending on type, stage, and size of company as well as the experience and background of the person in the role and who they are reporting to at a company. I like to tell people that my role is all about enabling and empowering everyone at my company to do their best work. Though, my coworkers like to describe me as the glue holding everything together or the woman steering the ship."

Jess Leonard, Gamesight: "A Chief of Staff’s primary role is to act as a force multiplier for a C-level principal. I think the Head of Ops generally acts a little more like a traditional head of a department, whereas a Chief of Staff may never have any direct reports or a department to lead... I’ve always been a hyper-organized person who thinks in systems and processes, and that’s exactly what Gamesight was looking for. If I recall, the job description stated they were looking for someone with, “a true appreciation for Monica Geller” who is definitely an important fixture in my life."

Simon Rodrigues, Fractional CoS: My job is to make my principal into a superhero. That means being their shadow problem-solver. In practice, that looks like: amplifying core messages through internal and external comms, making sure (the right) shit gets done, and being a sounding board.

The following roles are not operations leadership roles per se, but they are a crucial part of an ops team and a big part of what helps leaders be successful.

One of the biggest mistakes I see companies (especially early stage startups) make is to hire a senior operations pro for one of the roles above and then bog them down with a long list of admin duties.

Admin will always be a part of operations roles, but one of the most important jobs of a senior ops leader is to learn how to streamline that admin so they are doing (1) as little admin as possible, (2) only the most crucial pieces, and (3) handing it off as soon as possible.

Bogging down a Head of Operations or Chief of Staff with stuff that’s a better fit for a Virtual Assistant or Executive Assistant is a waste of your budget and it prevents you from fully utilizing the leader's expertise.

It's much better to staff your team with a high-level strategic leader and at least one person who thrives on details and execution.

Operations Managers

Operations Managers are often the glue that hold our organizations together! While they’re often involved in strategy at the team level (if not company level), they still spend the majority of their time planning and executing their own projects and so they are not operations leadership per se.

Operations Managers are often mid-level ops pros because the role is often seen as a stepping stone into operations leadership. However, this role can also be a great long-term fit for people who generally prefer an IC role but still want to contribute to the bigger picture.

At smaller startups, it’s not uncommon for an Operations Manager to be the only ops pro on the team, especially at an earlier stage company that hasn't really hit scale yet. Larger companies, meanwhile, might have a half-dozen Operations Managers at any given time, all of whom focus on their own projects.

Executive/Virtual/Admin Assistants

EAs and VAs, as they’re mostly commonly called, are definitely operations roles. And crucial ones at that!

These folks are almost exclusively focused on execution. Exact duties vary a little between Executive Assistants, Virtual Assistants, and Admin Assistants, but the objective is the same: their work supports your team in doing their best work, and frees up leadership to focus on their most crucial tasks. Assistants shouldn’t be managing people or driving strategy.

A lot of people think of these roles only as stepping stones to a “bigger” role, but that’s short-sighted. An experienced assistant can be an invaluable asset and, while they may not be operations leadership, they are a crucial element in helping ops leaders be successful.

Your Questions

• What skill or experience has best prepared you for your role?
• What advice do you have for someone who wants to move into operations leadership? How can they best prepare themselves for the role?

Answered By

What skill or experience has best prepared you for your role?

Clare: I’m not sure I was prepared for the [VP of Operations] role! I’ve always been a generalist looking outside the current scope of work to see the impacts and to analyze data to make informed decisions – perhaps it was that. Perhaps it is my love of problem solving and improvement. Throughout my career I’ve been able to observe keen leaders... and I knew I wanted my next role to be in Operations working with a dynamic CEO/President, I wanted the opportunity to look at accelerated growth as a positive problem to support, not to solve the problem, because accelerated growth is not a bad problem to solve, but to support with people and systems to ensure the growth can happen and be driven without exhausting the people.

Deanna: Hands down, it's been my issue identification and methodical organization skills. I define issue identification as the ability to quickly absorb the facts of a situation and identify the top 1-2 problems causing inefficiency, delay, and/or delivery.  Then skill to focus on those problems and come to solutions (or suggested solutions) by creating dialogue, action and a path to decision making. And methodical organization is exactly that - the ability to keep track of many things at once and not leave anything or anyone hanging. Prioritization is also a great sub-skill to have!  

Kristy: Many, many, many! Anything I do in life feels like it is preparing me more and more for my role. However, I was a property manager earlier in my career, and I was located in locations that were often faced with huge natural disasters, such as flooding, bush fires, or impacts like the GFC. This enabled the ability to be agile, adaptable, and respond with a crisis management framework. Ops, as much as we want it to be forward thinking, proactive work, it can very often be reactive, 'fight the fire' moments that define our careers.

Jess: I started my professional career as an independent petroleum landman. I had to create my own LLC and manage my own business and its finances. There was also no formal training for that position, so really quickly I had to get good at learning from those with expertise in my industry, doing research to find resources, and generally being an advocate for myself.

What advice do you have for someone who wants to move into operations leadership? How can they best prepare themselves for the role?

Jess: You need to be comfortable with ambiguity and find a way to stay organized in spite of that uncertainty. You need to feel okay about working in the background, doing things that the rest of the team might not notice or appreciate. It can be an isolating role at times, but as long as you maintain a solid relationship with your principal and create a network of peers, you’ll kick ass.

Kristy: Pace yourself - you need to be able to run at different speeds. Ops, especially the years when you are more the 'doer' than the leader, are very fast, sharp, big chunks of work. It's very easy to think this is what you need to be as a leader, but it is actually the opposite. You need to have space to think, ponder, and map back to a core issue, not always a solution. Find another gear other than GO, and keep working on that, then find another gear, until you have 3, 4, or 5 gears.

Clare: Identify strong leaders and watch, listen and learn from them. Be ready for continual change and be ok with that—whether it is people, personalities or systems. Pay attention to the details and data, use it to make solid decisions that you are sure of because others will look to you to make a decision and run with it. The decision doesn’t always have to be correct, and when it is not, make a change quickly and support it. You will not be right all the time and that is ok, growth from incorrect decisions is key.

Deanna: Be open to taking on duties and responsibilities a bit outside their comfort zone for the opportunity to join a company where they find alignment with culture, mission and values.  I initially took a role in People Ops and worked my way into BizOps and then Head of Ops... it's been a journey, but I've gained tremendous experience along the way.  The ability to work on different teams within a company is a great way to prepare for an ops leadership role.

Barrett: The breadth of knowledge you need across areas of any given business grows very rapidly the further up the ladder you go and, so, what I find for a lot of ops people who are kind of mid-career is that they'll typically have had one area of expertise, whether it's Finance, People, maybe even like some Biz Ops where they're kind of consulting across groups in a company... That's great and you're going to need a lot more than that as you continue to grow. So, I actually think Biz Ops people are often the ones with the best trajectory, because they get to see all the different units if they're positioned well. But my baseline advice would be, regardless of what kind of vertical of ops you've been in, get some rotational experience, even if you have to do it on your own time.

Simon: The best advice I was ever given was, "Go for it." Human brains are naturally risk averse; we evolved to avoid threats. That means that we often inflate the value of safe options and overlook the cost of inaction. When I ask peers and colleagues about their deepest regrets, they most often choose some version of inaction or failure to launch. We repeatedly underestimate the opportunity cost of inertia. I would rather try and fail than wonder “what if?”